Regarded as one of the finest free safeties to have ever played the game, he was a six-time Pro Bowl selection from 1983–1988, starting in five of them in his 11 years with the Chiefs. Few other Chiefs players, including Derrick Thomas, Will Shields, and Willie Lanier, have been selected to this number of Pro Bowls. He had six 100 tackle seasons in his eleven years as a member of the Chiefs, with a career total of 927 tackles. He was a 5 time All-Pro in 1983, 1984, 1985, 1986, and 1988. He was also a five-time 1st team All-AFC and two time 2nd team All-AFC selection. Cherry's 15 career fumble recoveries place him in a three-way tie for the Chiefs record. He ranks third on the Chiefs list of most interceptions, and is only the 26th player in the history of the NFL to reach the 50 interception plateau. In 1987, he was selected to the Chiefs 25 year All-Time Team.

In 1995, Cherry became a limited ownership partner in one of the NFL’s then-new expansion teams, the Jacksonville Jaguars. This made him the first minority owner of an NFL franchise in the league's history. Cherry is also a managing general partner with United Beverage, a local Anheuser-Busch distributor.